I am currently looking for an internship to gain practical experience in managing STRs.

Contractor management is one of the most challenging parts of the business.

I talk to our local Section 8 office frequently as a property manager and in the begin they made it VERY CLEAR that the minimums are to protect the landlord AND the tenant.Most likely, the tenants are not going to have excess cash flow or savings to cover any of the damage to your "upgrades". 

Buy 4 more properties - one approximately every 3 months, based on the following logic = always fill existing property with a tenant prior to moving on (I'm new, and this is my way of managing risk); build resources to purchase next property (I have pretty decent purchasing power right now through conventional lending with my current job, and I also have a private lender ready to loan on my next property, and I also get a quarterly commission check that provides a nice financial bump every 3 months); finding a property takes time, but it is worth it to find the right property in the neighborhoods I want to invest in, at the right price.

So, we found a property manager through a friend and fell into the business.In 2023 we decided the real estate thing might work, refinanced our property from 2009 and bought an additional rental property in the same area placed it with our current property manager… on purpose this time.

It can be more challenging to manage your calendar to keep space for the longer MTR bookings, though.

Obviously I’m in Canada so would need a property management company so that would add to the expenses, but I don’t know, something feels right about an investment like this.

Once you find your 1st property, hire a property manager.

They are expect property managers in Atlanta and can help you navigate this chaos. https://www.pmigeorgia.com/about

In terms of mitigating your risk - particularly if you buy a condo - consider a newer building, steel or masonry construction, a unit on Floor 3 or above where Flood insurance wouldn't be necessary, larger buildings where costs are spread amongst more owners, and buildings with a financially healthy HOA (track record of good management, reserves in the budget to cover large capital expenditures, etc).